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During the 1959–60 OHA season, he slipped on some garbage strewn onto the ice and fell back into the boards. He broke the fifth verterbra in his back and doctors were worried they might have to amputate his legs when blood clots ensued. Gilbert started his career with the Rangers after finishing his junior career with the Guelph Royals during the 1960–61 season.

It did not take long for Gilbert to become popular with the Garden faithful, and he did not disappoint as he rose in prominence as an NHL star. However, it was not without pain. In 1965–66, his career was nearly derailed when he went through a second spinal fusion operation.[1] This surgery was performed by Dr. Kazuo Yanagisawa. He lost half a season, but he bounced back with a strong season in 1966–1967. On February 24, 1968, he established himself as a bona fide NHL star as he scored four goals in a game against the Montreal Canadiens. It was stardom from there. The Ratelle-Hadfield-Gilbert line, called the GAG (Goal-A-Game) line, would terrorize enemy goaltenders for years. He was with Team Canada when they took on the Soviets in the 1972 Summit Series. He won the Bill Masterton Trophy in 1976 for his perseverance regarding his back troubles.

At the beginning of the 1977–78 NHL season, Gilbert and Rangers' General ManagerJohn Ferguson got into a contract dispute. When Gilbert finally returned to play, he was no longer the Gilbert of old. He retired after 19 seasons, having never led the Rangers to a Stanley Cup. His number 7 was retired by the Rangers on October 14, 1979; Gilbert's #7 was the first number to be retired by the Rangers. In 1969 he owned hist first restaurant. After his playing career was over, he opened his own restaurant 'Gilbert's' on Third Avenue near 75th street in Manhattan.